orgo question

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mgdent

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hi guys, in the chair configuration of cyclohexane, if you had an OH group and t-butyl on the same C, which would be equatorial? Basically, when you have 2 groups on the same C, which is axial and which is eq? I know eq is favored so the more bulky hindered group is eq but i havent seen them on the same carbon.

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I'm not sure if they would be on the same C due to steric hindrance. But if they are, I would go with the general rule of larger in eq, smaller in ax.

Just a guess though.
 
Unlikely to find two large groups on the same carbon, that'd be more of a reaction intermediate type thing...but just hypothetically I'd say the t-butyl group would be equatorial
 
If there were two groups on the same carbon, the bulkier group should be equatorial more often.

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hi guys, in the chair configuration of cyclohexane, if you had an OH group and t-butyl on the same C, which would be equatorial? Basically, when you have 2 groups on the same C, which is axial and which is eq? I know eq is favored so the more bulky hindered group is eq but i havent seen them on the same carbon.


t-butyl has equitorial priority, check chads vids, he has a great explanation for it
 
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